"""Anthropic handler mixin for HeadroomProxy.

Contains all Anthropic Messages API handlers including batch operations.
"""

from __future__ import annotations

import asyncio
import copy
import json
import logging
import os
import time
import uuid
from datetime import datetime
from typing import TYPE_CHECKING, Any

from headroom.proxy.stage_timer import StageTimer, emit_stage_timings_log

if TYPE_CHECKING:
    from fastapi import Request
    from fastapi.responses import Response, StreamingResponse

import httpx

from headroom.pipeline import PipelineStage, summarize_routing_markers
from headroom.proxy.auth_mode import classify_auth_mode, classify_client
from headroom.proxy.compression_decision import CompressionDecision
from headroom.proxy.helpers import extract_tags
from headroom.proxy.memory_decision import MemoryDecision
from headroom.proxy.memory_query import MemoryQuery
from headroom.proxy.outcome import RequestOutcome

logger = logging.getLogger("headroom.proxy")


class AnthropicHandlerMixin:
    """Mixin providing Anthropic API handler methods for HeadroomProxy."""

    @staticmethod
    def _tool_sort_key(tool: dict[str, Any]) -> tuple[str, str]:
        """Deterministic sort key for Anthropic/OpenAI-style tool definitions."""
        name = (
            str(tool.get("name", ""))
            or str(tool.get("function", {}).get("name", ""))
            or str(tool.get("type", ""))
        )
        try:
            canonical = json.dumps(tool, sort_keys=True, separators=(",", ":"), ensure_ascii=False)
        except Exception:
            canonical = str(tool)
        return (name, canonical)

    @staticmethod
    def _extract_anthropic_cache_ttl_metrics(usage: dict[str, Any] | None) -> tuple[int, int]:
        """Extract observed Anthropic cache-write TTL bucket usage.

        HeadroomProxy also inherits StreamingMixin, which exposes the same
        helper for SSE usage parsing. Keep this local copy so the Anthropic
        handler remains safe when tested or embedded without StreamingMixin.
        """
        if not isinstance(usage, dict):
            return (0, 0)
        cache_creation = usage.get("cache_creation")
        if not isinstance(cache_creation, dict):
            return (0, 0)
        return (
            int(cache_creation.get("ephemeral_5m_input_tokens", 0) or 0),
            int(cache_creation.get("ephemeral_1h_input_tokens", 0) or 0),
        )

    @classmethod
    def _sort_tools_deterministically(
        cls, tools: list[dict[str, Any]] | None
    ) -> list[dict[str, Any]] | None:
        """Return tools in deterministic order to preserve prompt-cache stability."""
        if not tools:
            return tools
        return sorted(tools, key=cls._tool_sort_key)

    @staticmethod
    def _compress_latest_user_turn_images_cache_safe(
        messages: list[dict[str, Any]],
        *,
        frozen_message_count: int,
        compressor: Any,
    ) -> list[dict[str, Any]]:
        """Compress images only in the latest non-frozen user turn.

        This avoids rewriting historical image bytes that may already be in the
        provider prefix cache.
        """
        if not messages:
            return messages

        target_idx = len(messages) - 1
        if target_idx < frozen_message_count:
            return messages
        target_msg = messages[target_idx]
        if target_msg.get("role") != "user":
            return messages
        content = target_msg.get("content")
        if not isinstance(content, list):
            return messages
        if not any(isinstance(block, dict) and block.get("type") == "image" for block in content):
            return messages

        compressed_one = compressor.compress([target_msg], provider="anthropic")
        if not compressed_one:
            return messages

        if compressed_one[0] == target_msg:
            return messages

        updated = list(messages)
        updated[target_idx] = compressed_one[0]
        return updated

    @staticmethod
    def _append_context_to_latest_non_frozen_user_turn(
        messages: list[dict[str, Any]],
        context_text: str,
        *,
        frozen_message_count: int,
    ) -> list[dict[str, Any]]:
        """Append context to the first text block of the latest non-frozen user turn.

        This is the canonical memory-injection path (P0-1 fix in PR-A2). The
        cache hot zone (system + frozen prefix) is never touched. Only the
        first text block of the latest user message is mutated, which is by
        definition the live zone.

        Returns the input list unchanged if no eligible user text block
        exists (e.g., the last message is an assistant turn or a tool
        result, or the user message has no text block).
        """
        if not messages or not context_text:
            return messages

        i = len(messages) - 1
        if i < frozen_message_count:
            return messages
        msg = messages[i]
        if msg.get("role") != "user":
            return messages

        content = msg.get("content", "")
        if isinstance(content, str):
            updated = list(messages)
            updated[i] = {**msg, "content": content + "\n\n" + context_text}
            return updated

        if isinstance(content, list) and content:
            # Append to the first text block of the latest user message.
            # Anthropic content blocks are dicts with a "type" field; the
            # text block has type "text" and a "text" field.
            new_content: list[dict[str, Any]] = []
            appended = False
            for block in content:
                if not appended and isinstance(block, dict) and block.get("type") == "text":
                    existing = block.get("text", "")
                    new_content.append({**block, "text": existing + "\n\n" + context_text})
                    appended = True
                else:
                    new_content.append(block)
            if appended:
                updated = list(messages)
                updated[i] = {**msg, "content": new_content}
                return updated

        return messages

    @staticmethod
    def _strict_previous_turn_frozen_count(
        messages: list[dict[str, Any]],
        base_frozen_count: int,
    ) -> int:
        """Freeze all prior turns; only the final turn is mutable.

        If the final message is not a user turn, freeze everything.
        """
        if not messages:
            return base_frozen_count
        final_idx = len(messages) - 1
        if messages[final_idx].get("role") == "user":
            return max(base_frozen_count, final_idx)
        return len(messages)

    @staticmethod
    def _restore_frozen_prefix(
        original_messages: list[dict[str, Any]],
        candidate_messages: list[dict[str, Any]],
        *,
        frozen_message_count: int,
    ) -> tuple[list[dict[str, Any]], int]:
        """Force frozen prefix bytes to match the original request exactly."""
        if frozen_message_count <= 0 or not original_messages:
            return candidate_messages, 0

        frozen = min(frozen_message_count, len(original_messages))
        restored = list(candidate_messages)

        # Defensive: if a transform dropped prefix messages, restore them.
        if len(restored) < frozen:
            return list(original_messages[:frozen]) + restored, frozen

        changed = 0
        for idx in range(frozen):
            if restored[idx] != original_messages[idx]:
                restored[idx] = original_messages[idx]
                changed += 1
        return restored, changed

    @staticmethod
    def _extract_cache_stable_delta(
        current_messages: list[dict[str, Any]],
        previous_original_messages: list[dict[str, Any]] | None,
        previous_forwarded_messages: list[dict[str, Any]] | None,
    ) -> tuple[list[dict[str, Any]], list[dict[str, Any]]] | None:
        """Return (stable_forwarded_prefix, appended_delta_messages) when safe.

        Safe means the prior original request is an exact message-prefix of the
        current original request. This lets us replay the exact forwarded bytes
        for historical context and only transform newly appended message suffixes.
        """
        if not previous_original_messages or previous_forwarded_messages is None:
            return None
        prefix_len = len(previous_original_messages)
        if len(current_messages) < prefix_len:
            return None
        if current_messages[:prefix_len] != previous_original_messages:
            return None
        return (
            copy.deepcopy(previous_forwarded_messages),
            copy.deepcopy(current_messages[prefix_len:]),
        )

    @staticmethod
    def _extract_cache_stable_last_message_suffix(
        current_messages: list[dict[str, Any]],
        previous_original_messages: list[dict[str, Any]] | None,
        previous_forwarded_messages: list[dict[str, Any]] | None,
    ) -> tuple[list[dict[str, Any]], dict[str, Any], list[dict[str, Any]]] | None:
        """Return append-only delta when only the latest message grew in place."""
        if not previous_original_messages or previous_forwarded_messages is None:
            return None
        if (
            len(current_messages) != len(previous_original_messages)
            or len(previous_forwarded_messages) != len(previous_original_messages)
            or not current_messages
        ):
            return None

        prefix_len = len(current_messages) - 1
        if (
            prefix_len > 0
            and current_messages[:prefix_len] != previous_original_messages[:prefix_len]
        ):
            return None

        current_last = current_messages[-1]
        previous_original_last = previous_original_messages[-1]
        previous_forwarded_last = previous_forwarded_messages[-1]
        if current_last.get("role") != previous_original_last.get("role") or current_last.get(
            "role"
        ) != previous_forwarded_last.get("role"):
            return None

        current_content = current_last.get("content")
        previous_original_content = previous_original_last.get("content")
        previous_forwarded_content = previous_forwarded_last.get("content")

        if (
            isinstance(current_content, str)
            and isinstance(previous_original_content, str)
            and isinstance(previous_forwarded_content, str)
            and current_content.startswith(previous_original_content)
        ):
            suffix = current_content[len(previous_original_content) :]
            delta_messages = []
            if suffix:
                delta_messages = [{**copy.deepcopy(current_last), "content": suffix}]
            return (
                copy.deepcopy(previous_forwarded_messages[:-1]),
                copy.deepcopy(previous_forwarded_last),
                delta_messages,
            )

        if (
            isinstance(current_content, list)
            and isinstance(previous_original_content, list)
            and isinstance(previous_forwarded_content, list)
            and len(current_content) >= len(previous_original_content)
            and current_content[: len(previous_original_content)] == previous_original_content
        ):
            delta_blocks = copy.deepcopy(current_content[len(previous_original_content) :])
            delta_messages = []
            if delta_blocks:
                delta_messages = [{**copy.deepcopy(current_last), "content": delta_blocks}]
            return (
                copy.deepcopy(previous_forwarded_messages[:-1]),
                copy.deepcopy(previous_forwarded_last),
                delta_messages,
            )
        return None

    @staticmethod
    def _merge_appended_message_delta(
        previous_forwarded_message: dict[str, Any],
        delta_forwarded_message: dict[str, Any] | None,
    ) -> dict[str, Any] | None:
        """Merge a compressed suffix back into the prior forwarded message."""
        if delta_forwarded_message is None:
            return copy.deepcopy(previous_forwarded_message)
        if previous_forwarded_message.get("role") != delta_forwarded_message.get("role"):
            return None

        previous_content = previous_forwarded_message.get("content")
        delta_content = delta_forwarded_message.get("content")
        if isinstance(previous_content, str) and isinstance(delta_content, str):
            return {
                **copy.deepcopy(previous_forwarded_message),
                "content": previous_content + delta_content,
            }
        if isinstance(previous_content, list) and isinstance(delta_content, list):
            return {
                **copy.deepcopy(previous_forwarded_message),
                "content": copy.deepcopy(previous_content) + copy.deepcopy(delta_content),
            }
        return None

    @staticmethod
    def _assistant_message_from_response_json(
        resp_json: dict[str, Any] | None,
    ) -> dict[str, Any] | None:
        if not resp_json:
            return None
        if resp_json.get("role") != "assistant":
            return None
        return {
            "role": "assistant",
            "content": copy.deepcopy(resp_json.get("content", "")),
        }

    async def handle_anthropic_messages(
        self,
        request: Request,
    ) -> Response | StreamingResponse:
        """Handle Anthropic /v1/messages endpoint."""
        if not hasattr(self, "pipeline_extensions"):
            from headroom.pipeline import PipelineExtensionManager

            self.pipeline_extensions = PipelineExtensionManager(discover=False)

        from fastapi import HTTPException
        from fastapi.responses import JSONResponse, Response

        from headroom.cache.compression_store import get_compression_store
        from headroom.ccr import CCRToolInjector
        from headroom.proxy.helpers import (
            MAX_MESSAGE_ARRAY_LENGTH,
            MAX_REQUEST_BODY_SIZE,
            BodyMutationTracker,
            _get_image_compressor,
            compute_turn_id,
            read_request_json_with_bytes,
        )
        from headroom.proxy.modes import is_cache_mode, is_token_mode
        from headroom.tokenizers import get_tokenizer
        from headroom.utils import extract_user_query

        start_time = time.time()
        request_id = await self._next_request_id()
        trace_session_id = uuid.uuid4().hex

        # Phase F PR-F1: classify auth mode at request entry. The result
        # is stored on `request.state` so downstream handlers (cache
        # gates, header injection, lossy-compressor gates) read it
        # without re-classifying. Pure function, well under 10us.
        auth_mode = classify_auth_mode(request.headers)
        request.state.auth_mode = auth_mode
        logger.debug(f"[{request_id}] auth_mode_classified mode={auth_mode.value}")

        # Unit 2: per-stage timings for the pre-upstream phase. The
        # finalizer emits one structured log line + Prometheus
        # observations even if the handler raises.
        stage_timer = StageTimer()
        pre_upstream_started_at = time.perf_counter()
        _stage_timings_emitted = False

        # Unit 4: bounded pre-upstream concurrency. When the proxy is
        # configured with a semaphore, acquire it before reading the
        # request body so a replay storm cannot starve ``/livez``, new
        # Codex WS opens, or the HTTP thread pool. The release happens
        # BEFORE we start streaming response bytes back to the client —
        # the semaphore must not be held for the whole response
        # lifetime. ``_release_pre_upstream_sem`` is idempotent and
        # called on every exit path (early 4xx return, upstream error,
        # exception, and just before each streaming handoff).
        pre_upstream_sem = getattr(self, "anthropic_pre_upstream_sem", None)
        _pre_upstream_sem_acquired = False

        def _release_pre_upstream_sem() -> None:
            nonlocal _pre_upstream_sem_acquired
            if _pre_upstream_sem_acquired and pre_upstream_sem is not None:
                _pre_upstream_sem_acquired = False
                pre_upstream_sem.release()

        async def _finalize_pre_upstream() -> None:
            """Release the pre-upstream semaphore and emit stage-timing metrics.

            Idempotent: safe to call multiple times. The PRIMARY action is
            releasing the Unit 4 pre-upstream semaphore via
            ``_release_pre_upstream_sem()`` (itself idempotent); emitting
            stage timings is secondary bookkeeping guarded by
            ``_stage_timings_emitted``. Doing both here (rather than only
            at explicit handoff sites) guarantees semaphore release on
            every exit path — early 4xx returns, security blocks, cache
            hits, upstream errors, streaming handoff.
            """
            nonlocal _stage_timings_emitted
            _release_pre_upstream_sem()
            if _stage_timings_emitted:
                return
            _stage_timings_emitted = True
            if "total_pre_upstream" not in stage_timer:
                stage_timer.record(
                    "total_pre_upstream",
                    (time.perf_counter() - pre_upstream_started_at) * 1000.0,
                )
            await emit_stage_timings_log(
                path="anthropic_messages",
                request_id=request_id,
                session_id=trace_session_id,
                stage_timer=stage_timer,
                expected_stages=(
                    "pre_upstream_wait",
                    "read_request_json",
                    "deep_copy",
                    "compression_first_stage",
                    "memory_context",
                    "upstream_connect",
                    "upstream_first_byte",
                    "total_pre_upstream",
                ),
                metrics=getattr(self, "metrics", None),
            )

        if pre_upstream_sem is not None:
            _wait_started_at = time.perf_counter()
            _acquire_timeout_seconds = self.config.anthropic_pre_upstream_acquire_timeout_seconds
            try:
                await asyncio.wait_for(
                    pre_upstream_sem.acquire(),
                    timeout=_acquire_timeout_seconds,
                )
            except asyncio.TimeoutError:
                _wait_ms = (time.perf_counter() - _wait_started_at) * 1000.0
                stage_timer.record("pre_upstream_wait", _wait_ms)
                logger.warning(
                    "[%s] Anthropic pre-upstream queue saturated after %.2f ms "
                    "(timeout=%.1fs, session_id=%s)",
                    request_id,
                    _wait_ms,
                    _acquire_timeout_seconds,
                    trace_session_id,
                )
                await _finalize_pre_upstream()
                return JSONResponse(
                    status_code=503,
                    headers={"Retry-After": str(max(1, int(_acquire_timeout_seconds) + 1))},
                    content={
                        "type": "error",
                        "error": {
                            "type": "service_unavailable",
                            "message": (
                                "Anthropic pre-upstream queue is saturated. Please retry shortly."
                            ),
                        },
                    },
                )
            _pre_upstream_sem_acquired = True
            _wait_ms = (time.perf_counter() - _wait_started_at) * 1000.0
            stage_timer.record("pre_upstream_wait", _wait_ms)
            if _wait_ms > 100.0:
                logger.info(
                    "[%s] pre_upstream_wait_ms=%.2f session_id=%s "
                    "(anthropic pre-upstream semaphore contention)",
                    request_id,
                    _wait_ms,
                    trace_session_id,
                )
        else:
            stage_timer.record("pre_upstream_wait", 0.0)

        try:
            # Check request body size
            content_length = request.headers.get("content-length")
            if content_length and int(content_length) > MAX_REQUEST_BODY_SIZE:
                await _finalize_pre_upstream()
                return JSONResponse(
                    status_code=413,
                    content={
                        "type": "error",
                        "error": {
                            "type": "request_too_large",
                            "message": f"Request body too large. Maximum size is {MAX_REQUEST_BODY_SIZE // (1024 * 1024)}MB",
                        },
                    },
                )

            # Parse request — capture both the parsed dict AND the original
            # bytes so the forwarder can pick byte-faithful passthrough when
            # nothing mutated the body (PR-A3, fixes P0-2). The mutation
            # tracker is updated by every transform site that touches the
            # body (image compression, memory injection, message rewriting,
            # tool sorting, etc.).
            body_mutation_tracker = BodyMutationTracker()
            try:
                async with stage_timer.measure("read_request_json"):
                    body, original_body_bytes = await read_request_json_with_bytes(request)
            except (json.JSONDecodeError, ValueError) as e:
                await _finalize_pre_upstream()
                return JSONResponse(
                    status_code=400,
                    content={
                        "type": "error",
                        "error": {
                            "type": "invalid_request_error",
                            "message": f"Invalid request body: {e!s}",
                        },
                    },
                )
            model = body.get("model", "unknown")
            messages = body.get("messages", [])
            with stage_timer.measure("deep_copy"):
                original_client_messages = copy.deepcopy(messages)
            input_event = self.pipeline_extensions.emit(
                PipelineStage.INPUT_RECEIVED,
                operation="proxy.request",
                request_id=request_id,
                provider="anthropic",
                model=model,
                messages=messages,
                tools=body.get("tools"),
                metadata={"path": "/v1/messages", "stream": body.get("stream", False)},
            )
            if input_event.messages is not None:
                messages = input_event.messages
                with stage_timer.measure("deep_copy"):
                    original_client_messages = copy.deepcopy(messages)
            if input_event.tools is not None:
                body["tools"] = input_event.tools

            # Validate message array size
            if len(messages) > MAX_MESSAGE_ARRAY_LENGTH:
                await _finalize_pre_upstream()
                return JSONResponse(
                    status_code=400,
                    content={
                        "type": "error",
                        "error": {
                            "type": "invalid_request_error",
                            "message": f"Message array too large ({len(messages)} messages). "
                            f"Maximum is {MAX_MESSAGE_ARRAY_LENGTH}.",
                        },
                    },
                )

            stream = body.get("stream", False)

            # Bypass: skip ALL compression, TOIN learning, and CCR injection
            # when the caller explicitly opts out via header.
            # Prevents Headroom from corrupting sub-agent API calls
            # (e.g., Claude Code sub-agents that inherit ANTHROPIC_BASE_URL).
            _bypass = (
                request.headers.get("x-headroom-bypass", "").lower() == "true"
                or request.headers.get("x-headroom-mode", "").lower() == "passthrough"
            )
            if _bypass:
                logger.info(f"[{request_id}] Bypass: skipping compression (header)")

            # NOTE: Upstream temporarily disabled broad image compression due to
            # token-counting inaccuracies. We only compress the latest non-frozen
            # user turn later in this handler to preserve Anthropic prefix caching.
            # Extract headers and tags
            headers = dict(request.headers.items())
            headers.pop("host", None)
            headers.pop("content-length", None)
            # Strip accept-encoding so httpx negotiates its own encoding.
            # Edge proxies (Cloudflare Workers, etc.) may forward "br, zstd" which
            # the upstream can honor; if httpx lacks brotli support the response
            # body is undecipherable → 502.
            headers.pop("accept-encoding", None)
            tags = extract_tags(headers)
            # Identify the harness (codex / claude-code / aider / etc.)
            # from User-Agent or X-Client. Surfaced via the funnel into
            # PERF logs and RequestLog.tags — see RequestOutcome.client.
            client = classify_client(headers)
            # PR-A5 (P5-49): strip internal x-headroom-* from upstream-bound
            # headers AFTER `_extract_tags` reads them. Inbound bypass gating
            # uses `request.headers.get(...)` directly above; memory user-id
            # is read from `request.headers` below if needed. From this
            # point on, `headers` is the upstream-bound copy.
            from headroom.proxy.helpers import _strip_internal_headers, log_outbound_headers

            _pre_strip_count = sum(1 for k in headers if k.lower().startswith("x-headroom-"))
            headers = _strip_internal_headers(headers)
            log_outbound_headers(
                forwarder="anthropic_messages",
                stripped_count=_pre_strip_count
                - sum(1 for k in headers if k.lower().startswith("x-headroom-")),
                request_id=request_id,
            )

            # Subscription tracker: notify on OAuth requests (not API-key requests)
            _auth_header = headers.get("authorization", "")
            if _auth_header.startswith("Bearer ") and not _auth_header.startswith(
                "Bearer sk-ant-api"
            ):
                from headroom.subscription.tracker import (
                    get_subscription_tracker as _get_sub_tracker,
                )

                _sub_tracker = _get_sub_tracker()
                if _sub_tracker is not None:
                    _sub_tracker.notify_active(_auth_header)

            # Rate limiting
            if self.rate_limiter:
                api_key = headers.get("x-api-key", "")
                if not api_key:
                    auth = headers.get("authorization", "")
                    if auth.startswith("Bearer "):
                        api_key = auth[7:]
                client_ip = request.client.host if request.client else "unknown"
                rate_key = f"{api_key[:16]}:{client_ip}" if api_key else client_ip
                allowed, wait_seconds = await self.rate_limiter.check_request(rate_key)
                if not allowed:
                    await self.metrics.record_rate_limited(provider="anthropic")
                    # Unit 4: release the pre-upstream semaphore before we
                    # bail out of the handler via HTTPException — FastAPI's
                    # exception handler will NOT run our ``finally``.
                    await _finalize_pre_upstream()
                    raise HTTPException(
                        status_code=429,
                        detail=f"Rate limited. Retry after {wait_seconds:.1f}s",
                        headers={"Retry-After": str(int(wait_seconds) + 1)},
                    )

            # Budget check
            if self.cost_tracker:
                allowed, remaining = self.cost_tracker.check_budget()
                if not allowed:
                    # Unit 4: release the pre-upstream semaphore before we
                    # bail out of the handler via HTTPException.
                    await _finalize_pre_upstream()
                    raise HTTPException(
                        status_code=429,
                        detail=f"Budget exceeded for {self.config.budget_period} period",
                    )

            # Memory: Get user ID when memory is enabled (fallback to "default" for simple DevEx).
            # Reads `request.headers` directly because the local `headers` dict was
            # stripped of `x-headroom-*` above for the upstream-bound copy (PR-A5).
            memory_user_id: str | None = None
            memory_request_ctx = None
            if self.memory_handler:
                memory_user_id = request.headers.get(
                    "x-headroom-user-id",
                    os.environ.get("USER", os.environ.get("USERNAME", "default")),
                )
                # Per-project memory routing (GH #462). Build the context
                # once here so save / search / inject all resolve against
                # the same workspace. Tier order: explicit project-id /
                # cwd headers → CLI override → system prompt env block.
                from headroom.memory.storage_router import (
                    RequestContext as _MemRequestContext,
                )
                from headroom.memory.storage_router import (
                    extract_system_prompt as _extract_sys_prompt,
                )

                memory_request_ctx = _MemRequestContext(
                    headers=dict(request.headers),
                    system_prompt=_extract_sys_prompt(body),
                    base_user_id=memory_user_id,
                    project_root_override=(
                        getattr(self.memory_handler.config, "project_root_override", "") or None
                    ),
                )

            # Canonical memory-injection gate. Reads `request.headers`
            # so bypass detection sees the original inbound (the local
            # `headers` dict was stripped of x-headroom-* above).
            # Replaces the pre-PR-this raw `if self.memory_handler and
            # memory_user_id:` conjunction that silently ignored
            # `x-headroom-bypass: true` and mutated request bytes
            # under the user's "don't touch my bytes" signal.
            from headroom.proxy.helpers import get_memory_injection_mode

            memory_decision = MemoryDecision.decide(
                headers=request.headers,
                memory_handler=self.memory_handler,
                memory_user_id=memory_user_id,
                mode_name=get_memory_injection_mode(),
            )
            memory_decision.apply_to_tags(tags)

            # Check cache (non-streaming only)
            cache_hit = False
            if self.cache and not stream:
                cached = await self.cache.get(messages, model)
                if cached:
                    cache_hit = True
                    self.pipeline_extensions.emit(
                        PipelineStage.INPUT_CACHED,
                        operation="proxy.request",
                        request_id=request_id,
                        provider="anthropic",
                        model=model,
                        messages=messages,
                        metadata={"cache_hit": True, "path": "/v1/messages"},
                    )
                    optimization_latency = (time.time() - start_time) * 1000

                    # Response-cache hit: response body came from
                    # Headroom's semantic cache, not the upstream
                    # provider. ``from_response_cache=True`` is a
                    # distinct signal from `cache_read_tokens > 0`
                    # (which means upstream-prompt-cache hit). Dashboards
                    # can split the two; the funnel collapses them into
                    # the single `cached` boolean for Prometheus.
                    await self._record_request_outcome(
                        RequestOutcome(
                            request_id=request_id,
                            provider="anthropic",
                            model=model,
                            original_tokens=0,
                            optimized_tokens=0,
                            output_tokens=0,
                            tokens_saved=0,
                            attempted_input_tokens=0,
                            from_response_cache=True,
                            total_latency_ms=optimization_latency,
                            overhead_ms=optimization_latency,
                            num_messages=len(messages),
                            tags=tags,
                            client=client,
                        )
                    )

                    # Remove compression headers from cached response
                    response_headers = dict(cached.response_headers)
                    response_headers.pop("content-encoding", None)
                    response_headers.pop("content-length", None)

                    # Unit 4: release the pre-upstream semaphore on cache
                    # hit — no upstream call will happen.
                    await _finalize_pre_upstream()
                    return Response(
                        content=cached.response_body,
                        headers=response_headers,
                        media_type="application/json",
                    )

            # Count original tokens
            tokenizer = get_tokenizer(model)
            original_tokens = tokenizer.count_messages(messages)

            # Enterprise Security: scan request before compression
            _security_ctx = None
            if self.security:
                try:
                    messages, _security_ctx = self.security.scan_request(
                        messages,
                        {
                            "provider": "anthropic",
                            "model": model,
                            "request_id": str(request_id),
                            "user_id": headers.get("x-api-key", "")[:16],
                        },
                    )
                except Exception as e:
                    if hasattr(e, "reason"):
                        from fastapi.responses import JSONResponse as _JSONResp

                        # Unit 4: release the pre-upstream semaphore on
                        # security block — no upstream call will happen.
                        await _finalize_pre_upstream()
                        return _JSONResp(
                            status_code=403,
                            content={
                                "type": "error",
                                "error": {
                                    "type": "security_block",
                                    "message": str(e),
                                },
                            },
                        )
                    logger.warning(f"[{request_id}] Security scan error: {e}")

            # Hook: pre_compress — let hooks modify messages before compression

            if self.config.hooks and not is_cache_mode(self.config.mode):
                from headroom.hooks import CompressContext

                _hook_ctx = CompressContext(
                    model=model,
                    user_query=extract_user_query(messages),
                    provider="anthropic",
                )
                try:
                    messages = self.config.hooks.pre_compress(messages, _hook_ctx)
                except Exception as e:
                    logger.debug(f"[{request_id}] pre_compress hook error: {e}")
            else:
                _hook_ctx = None

            # Apply optimization
            transforms_applied = []
            pipeline_timing: dict[str, float] = {}
            waste_signals_dict: dict[str, int] | None = None
            optimized_messages = messages
            optimized_tokens = original_tokens

            # Get prefix cache tracker for this session
            session_id = self.session_tracker_store.compute_session_id(request, model, messages)
            prefix_tracker = self.session_tracker_store.get_or_create(session_id, "anthropic")
            frozen_message_count = prefix_tracker.get_frozen_message_count()
            if is_cache_mode(self.config.mode):
                frozen_message_count = self._strict_previous_turn_frozen_count(
                    original_client_messages,
                    frozen_message_count,
                )

            # PR-A6 (P5-50, preps P0-6): session-sticky `anthropic-beta` merge.
            # Read the client's beta value (note: anthropic-beta is NOT
            # an x-headroom-* header so it survived the A5 strip), union
            # with previously-seen tokens for this session, and update
            # the tracker. Memory-injection (below at line ~1244) uses
            # `merge_anthropic_beta` to add `context-management-2025-06-27`
            # on top of the sticky baseline. Order matters: session-sticky
            # FIRST so we have the canonical baseline; memory injection
            # adds Headroom-required tokens AFTER.
            from headroom.proxy.helpers import (
                get_session_beta_tracker,
                log_beta_header_merge,
            )

            _client_beta_value = headers.get("anthropic-beta")
            _client_beta_count = (
                len([t for t in (_client_beta_value or "").split(",") if t.strip()])
                if _client_beta_value
                else 0
            )
            _sticky_beta_value = get_session_beta_tracker().record_and_get_sticky_betas(
                provider="anthropic",
                session_id=session_id,
                client_value=_client_beta_value,
            )
            _sticky_beta_count = (
                len([t for t in _sticky_beta_value.split(",") if t.strip()])
                if _sticky_beta_value
                else 0
            )
            if _sticky_beta_value and _sticky_beta_value != (_client_beta_value or ""):
                headers["anthropic-beta"] = _sticky_beta_value
            elif not _sticky_beta_value and "anthropic-beta" in headers:
                # Sticky value can only equal "" when both client and
                # session are empty; preserve the (absent) client state.
                pass
            log_beta_header_merge(
                provider="anthropic",
                session_id=session_id,
                client_betas_count=_client_beta_count,
                sticky_betas_count=_sticky_beta_count,
                headroom_added=[],
                request_id=request_id,
            )

            # In cache mode, avoid rewriting any message body bytes. The latest user
            # turn becomes historical on the next request, so even "latest turn only"
            # rewrites can invalidate the next cache read when the client resends the
            # original transcript.
            #
            # Bypass / image_optimize / messages gating routes through
            # ImageCompressionDecision for uniformity with CompressionDecision +
            # MemoryDecision. The cache_mode check stays inline because it's
            # Anthropic-specific (sites in openai.py / gemini.py don't have it).
            from headroom.proxy.image_compression_decision import ImageCompressionDecision

            _image_decision = ImageCompressionDecision.decide(
                headers=request.headers, config=self.config, messages=messages
            )
            _image_decision.apply_to_tags(tags)
            if _image_decision.should_compress and not is_cache_mode(self.config.mode):
                compressor = None
                try:
                    compressor = _get_image_compressor()
                    if compressor and compressor.has_images(messages):
                        messages = compressor.compress(messages, provider="anthropic")
                        body_mutation_tracker.mark_mutated("image_compression")
                        if compressor.last_result:
                            logger.info(
                                f"Image compression: {compressor.last_result.technique.value} "
                                f"({compressor.last_result.savings_percent:.0f}% saved, "
                                f"{compressor.last_result.original_tokens} -> "
                                f"{compressor.last_result.compressed_tokens} tokens)"
                            )
                finally:
                    if compressor and hasattr(compressor, "close"):
                        compressor.close()

            _compression_failed = False
            original_messages = messages  # Preserve for 400-retry fallback
            _decision = CompressionDecision.decide(
                headers=request.headers,
                config=self.config,
                usage_reporter=self.usage_reporter,
                messages=messages,
            )
            _decision.apply_to_tags(tags)
            if not _decision.should_compress:
                logger.info(
                    f"[{request_id}] Compression skipped: reason={_decision.passthrough_reason}"
                )
            if _decision.should_compress:
                try:
                    from headroom.proxy.helpers import COMPRESSION_TIMEOUT_SECONDS

                    context_limit = self.anthropic_provider.get_context_limit(model)
                    result = None
                    biases = (
                        self.config.hooks.compute_biases(messages, _hook_ctx)
                        if self.config.hooks and _hook_ctx is not None
                        else None
                    )

                    # F2.1 c5/5: derive the per-request CompressionPolicy
                    # from the auth_mode classified at request entry. The
                    # policy short-circuits CacheAligner for subscription
                    # users (closes the cache-instability complaints in
                    # #327/#388). When the enforcement env var is off, the
                    # policy collapses to PAYG so behaviour is unchanged.
                    # Hoisted here so all three pipeline.apply call sites
                    # (token / non-cache / cache-delta) see the same policy.
                    from headroom.transforms.compression_policy import resolve_policy

                    compression_policy = resolve_policy(getattr(request.state, "auth_mode", None))

                    if is_token_mode(self.config.mode):
                        comp_cache = self._get_compression_cache(session_id)

                        # Zone 1: Swap cached compressed versions into working copy
                        working_messages = comp_cache.apply_cached(messages)

                        # Re-freeze boundary: consecutive stable messages from start.
                        # Safety: never freeze beyond provider-confirmed cached prefix.
                        # `prefix_tracker.frozen_message_count` (set above) is the
                        # AUTHORITATIVE positional truth — derived from Anthropic's
                        # `cache_read_input_tokens` response. `compute_frozen_count`
                        # provides a defensive lower bound from local cache state.
                        # Use the smaller; never extend past what Anthropic actually
                        # has cached.
                        #
                        # Issue #327: a previous version walked past
                        # `prefix_tracker.frozen_message_count` whenever an upcoming
                        # tool_result's content-hash matched `_stable_hashes` or
                        # `should_defer_compression` returned True. That conflated
                        # content equality with positional cache membership: the
                        # prefix cache is positional (bytes 0..K cached, anything
                        # past K is fresh), but `_stable_hashes` is content-keyed
                        # and grows unbounded. On long Claude Code sessions where
                        # tool_result content rhymes across turns (repeated system
                        # prompts, repeated file reads, etc.), the walker advanced
                        # `frozen_message_count` to `len(messages)` and the
                        # pipeline produced `transforms_applied=[]` on 73% of
                        # requests. The walker has been removed; trust
                        # `prefix_tracker` clamped by `compute_frozen_count`.
                        cache_frozen_count = comp_cache.compute_frozen_count(messages)
                        frozen_message_count = min(frozen_message_count, cache_frozen_count)
                        # Record all tool_results in the verified frozen prefix as stable
                        comp_cache.mark_stable_from_messages(messages, frozen_message_count)

                        async with stage_timer.measure("compression_first_stage"):
                            result = await self._run_compression_in_executor(
                                lambda: self.anthropic_pipeline.apply(
                                    messages=working_messages,
                                    model=model,
                                    model_limit=context_limit,
                                    context=extract_user_query(working_messages),
                                    frozen_message_count=frozen_message_count,
                                    biases=biases,
                                    request_id=request_id,
                                    compression_policy=compression_policy,
                                ),
                                timeout=COMPRESSION_TIMEOUT_SECONDS,
                            )

                        # Cache newly compressed messages (index-aligned diff)
                        if result.messages != working_messages:
                            comp_cache.update_from_result(messages, result.messages)

                        # Always use pipeline result — Zone 1 swaps are already applied
                        optimized_messages = result.messages
                        transforms_applied = result.transforms_applied
                        pipeline_timing = result.timing
                        # Issue #327 / Bug 3: pipeline.apply uses the provider-
                        # side tokenizer (AnthropicProvider tiktoken estimator),
                        # which counts ~25% higher than the proxy-side
                        # EstimatingTokenCounter used to set `original_tokens`
                        # at line 634. Reusing `result.tokens_after` here
                        # produced an apples-vs-oranges comparison against
                        # `original_tokens` in the inflation guard below
                        # (line ~901): even after a real 12% compression the
                        # provider-tokenizer figure was higher than the proxy-
                        # tokenizer baseline, triggering a spurious revert.
                        # Recount optimized_messages with the proxy tokenizer
                        # so original_tokens vs optimized_tokens is self-
                        # consistent. The recount cost (~ms on a 50K-token
                        # request) is paid once per request and is dwarfed by
                        # the upstream call latency.
                        optimized_tokens = tokenizer.count_messages(optimized_messages)
                    elif not is_cache_mode(self.config.mode):
                        async with stage_timer.measure("compression_first_stage"):
                            result = await self._run_compression_in_executor(
                                lambda: self.anthropic_pipeline.apply(
                                    messages=messages,
                                    model=model,
                                    model_limit=context_limit,
                                    context=extract_user_query(messages),
                                    frozen_message_count=frozen_message_count,
                                    biases=biases,
                                    request_id=request_id,
                                    compression_policy=compression_policy,
                                ),
                                timeout=COMPRESSION_TIMEOUT_SECONDS,
                            )

                        if result.messages != messages:
                            optimized_messages = result.messages
                            transforms_applied = result.transforms_applied
                            pipeline_timing = result.timing
                            original_tokens = result.tokens_before
                            optimized_tokens = result.tokens_after
                    else:
                        previous_original_messages = prefix_tracker.get_last_original_messages()
                        previous_forwarded_messages = prefix_tracker.get_last_forwarded_messages()
                        delta = self._extract_cache_stable_delta(
                            original_client_messages,
                            previous_original_messages,
                            previous_forwarded_messages,
                        )
                        if delta is not None:
                            stable_forwarded_prefix, delta_messages = delta
                            if delta_messages:
                                result = await self._run_compression_in_executor(
                                    lambda: self.anthropic_pipeline.apply(
                                        messages=delta_messages,
                                        model=model,
                                        model_limit=context_limit,
                                        context=extract_user_query(delta_messages),
                                        frozen_message_count=0,
                                        biases=biases,
                                        request_id=request_id,
                                        compression_policy=compression_policy,
                                    ),
                                    timeout=COMPRESSION_TIMEOUT_SECONDS,
                                )
                                optimized_messages = stable_forwarded_prefix + result.messages
                                transforms_applied = result.transforms_applied
                                pipeline_timing = result.timing
                                optimized_tokens = tokenizer.count_messages(optimized_messages)
                            else:
                                optimized_messages = stable_forwarded_prefix
                                optimized_tokens = tokenizer.count_messages(optimized_messages)
                        else:
                            # Conservative rule for cache mode:
                            # only replay exact stable message-prefix extensions.
                            # In-message append rewriting is deferred until we can
                            # prove it is perfectly replayable across future turns.
                            optimized_messages = messages
                            optimized_tokens = original_tokens

                    if result and result.waste_signals:
                        waste_signals_dict = result.waste_signals.to_dict()
                except Exception as e:
                    # Include type so TimeoutError vs other failures is distinguishable
                    # in bug reports — str(asyncio.TimeoutError()) is empty otherwise.
                    logger.warning(f"[{request_id}] Optimization failed: {type(e).__name__}: {e}")
                    # Flag compression failure for observability
                    _compression_failed = True

            # Guard: if "optimization" inflated tokens, revert to originals.
            # Skip in cache mode where prefix-stability may legitimately shift counts.
            if optimized_tokens > original_tokens and not is_cache_mode(self.config.mode):
                logger.warning(
                    f"[{request_id}] Optimization inflated tokens "
                    f"({original_tokens} -> {optimized_tokens}), reverting to original messages"
                )
                optimized_messages = original_messages
                optimized_tokens = original_tokens
                transforms_applied = []

            tokens_saved = max(0, original_tokens - optimized_tokens)
            optimization_latency = (time.time() - start_time) * 1000

            routing_markers = summarize_routing_markers(transforms_applied)
            if routing_markers:
                routed_event = self.pipeline_extensions.emit(
                    PipelineStage.INPUT_ROUTED,
                    operation="proxy.request",
                    request_id=request_id,
                    provider="anthropic",
                    model=model,
                    messages=optimized_messages,
                    metadata={
                        "routing_markers": routing_markers,
                        "transforms_applied": transforms_applied,
                    },
                )
                if routed_event.messages is not None:
                    previous_optimized_messages = optimized_messages
                    optimized_messages = routed_event.messages
                    if routed_event.messages is not previous_optimized_messages:
                        optimized_tokens = tokenizer.count_messages(optimized_messages)
                        tokens_saved = max(0, original_tokens - optimized_tokens)

            compressed_event = self.pipeline_extensions.emit(
                PipelineStage.INPUT_COMPRESSED,
                operation="proxy.request",
                request_id=request_id,
                provider="anthropic",
                model=model,
                messages=optimized_messages,
                metadata={
                    "tokens_before": original_tokens,
                    "tokens_after": optimized_tokens,
                    "transforms_applied": transforms_applied,
                },
            )
            if compressed_event.messages is not None:
                previous_optimized_messages = optimized_messages
                optimized_messages = compressed_event.messages
                if compressed_event.messages is not previous_optimized_messages:
                    optimized_tokens = tokenizer.count_messages(optimized_messages)
                    tokens_saved = max(0, original_tokens - optimized_tokens)

            # Hook: post_compress — let hooks observe compression results
            if self.config.hooks and tokens_saved > 0:
                from headroom.hooks import CompressEvent

                try:
                    self.config.hooks.post_compress(
                        CompressEvent(
                            tokens_before=original_tokens,
                            tokens_after=optimized_tokens,
                            tokens_saved=tokens_saved,
                            compression_ratio=tokens_saved / original_tokens
                            if original_tokens > 0
                            else 0,
                            transforms_applied=transforms_applied,
                            model=model,
                            user_query=_hook_ctx.user_query if self.config.hooks else "",
                            provider="anthropic",
                        )
                    )
                except Exception as e:
                    logger.debug(f"[{request_id}] post_compress hook error: {e}")

            # CCR Tool Injection: Inject retrieval tool if compression occurred
            # OR if this session has previously done CCR (PR-B7 sticky-on).
            # The legacy `CCRToolInjector` flips on/off based on the *current*
            # request's compressed-content presence, busting cache every flip.
            # We now route the tool-list update through
            # `apply_session_sticky_ccr_tool`, which once-on/always-on per
            # `SessionCcrTracker`. System-instruction injection keeps its
            # existing per-request scan (it lives in the system prompt, which
            # is the cache hot zone — gated separately by the
            # `frozen_message_count > 0` guard below).
            tools = body.get("tools")
            _original_tools = tools  # Preserve for diagnostic / future retry
            if (
                self.config.ccr_inject_tool or self.config.ccr_inject_system_instructions
            ) and not _bypass:
                inject_system_instructions = self.config.ccr_inject_system_instructions
                if inject_system_instructions and frozen_message_count > 0:
                    logger.info(
                        f"[{request_id}] CCR: skipping system instruction injection "
                        f"(frozen prefix={frozen_message_count}) to preserve cache"
                    )
                    inject_system_instructions = False
                inject_tool = self.config.ccr_inject_tool
                if inject_tool and frozen_message_count > 0:
                    logger.info(
                        f"[{request_id}] CCR: deferring tool injection "
                        f"(frozen prefix={frozen_message_count}) to preserve cache"
                    )
                    inject_tool = False
                # Scan for compression markers + maybe inject system instructions.
                # Tool-list injection is handled separately via the sticky helper.
                injector = CCRToolInjector(
                    provider="anthropic",
                    inject_tool=False,  # routed through sticky helper below
                    inject_system_instructions=inject_system_instructions,
                )
                injector.scan_for_markers(optimized_messages)
                if inject_system_instructions and injector.has_compressed_content:
                    optimized_messages = injector.inject_into_system_message(optimized_messages)

                # Sticky-on tool registration (PR-B7): always inject the
                # retrieval tool once a session has done CCR, regardless
                # of whether THIS turn produced compressed content.
                if inject_tool:
                    from headroom.proxy.helpers import apply_session_sticky_ccr_tool

                    tools, ccr_tool_injected = apply_session_sticky_ccr_tool(
                        provider="anthropic",
                        session_id=session_id,
                        request_id=request_id,
                        existing_tools=tools,
                        has_compressed_content_this_turn=injector.has_compressed_content,
                    )
                    if ccr_tool_injected:
                        logger.debug(
                            f"[{request_id}] CCR: tool registered (session={session_id}, "
                            f"compressed_this_turn={injector.has_compressed_content}, "
                            f"hashes_seen={len(injector.detected_hashes)})"
                        )

                if injector.has_compressed_content:
                    # Track compression in context tracker for multi-turn awareness
                    if self.ccr_context_tracker:
                        self._turn_counter += 1
                        for hash_key in injector.detected_hashes:
                            # Get compression metadata from store
                            store = get_compression_store()
                            entry = store.get_metadata(hash_key)
                            if entry:
                                self.ccr_context_tracker.track_compression(
                                    hash_key=hash_key,
                                    turn_number=self._turn_counter,
                                    tool_name=entry.get("tool_name"),
                                    original_count=entry.get("original_item_count", 0),
                                    compressed_count=entry.get("compressed_item_count", 0),
                                    query_context=entry.get("query_context", ""),
                                    sample_content=entry.get("compressed_content", "")[:500],
                                )

            # CCR Proactive Expansion: Check if current query needs expanded context
            if self.ccr_context_tracker and self.config.ccr_proactive_expansion:
                # Extract user query from messages
                user_query = ""
                for msg in reversed(messages):
                    if msg.get("role") == "user":
                        content = msg.get("content", "")
                        if isinstance(content, str):
                            user_query = content
                        elif isinstance(content, list):
                            for block in content:
                                if isinstance(block, dict) and block.get("type") == "text":
                                    user_query = block.get("text", "")
                                    break
                        break

                if user_query:
                    recommendations = self.ccr_context_tracker.analyze_query(
                        user_query, self._turn_counter
                    )
                    if recommendations:
                        expansions = self.ccr_context_tracker.execute_expansions(recommendations)
                        if expansions:
                            # Add expanded context to the system message or as additional context
                            expansion_text = self.ccr_context_tracker.format_expansions_for_context(
                                expansions
                            )
                            logger.info(
                                f"[{request_id}] CCR: Proactively expanded {len(expansions)} context(s) "
                                f"based on query relevance"
                            )
                            if is_cache_mode(self.config.mode):
                                logger.info(
                                    f"[{request_id}] CCR: skipping proactive expansion append "
                                    "in cache mode to preserve next-turn prefix stability"
                                )
                            else:
                                optimized_messages = (
                                    self._append_context_to_latest_non_frozen_user_turn(
                                        optimized_messages,
                                        expansion_text,
                                        frozen_message_count=frozen_message_count,
                                    )
                                )

            # Traffic Learner: Extract patterns from inbound tool results
            if self.traffic_learner:
                try:
                    # Wire backend on first use (lazy init after memory handler is ready)
                    if (
                        self.traffic_learner._backend is None
                        and self.memory_handler
                        and self.memory_handler.initialized
                        and self.memory_handler.backend
                    ):
                        self.traffic_learner.set_backend(self.memory_handler.backend)

                    # Extract tool results from messages and learn from them
                    tool_results = self.traffic_learner.extract_tool_results_from_messages(
                        optimized_messages
                    )
                    for tr in tool_results[-5:]:  # Only recent results
                        await self.traffic_learner.on_tool_result(
                            tool_name=tr["tool_name"],
                            tool_input=tr["input"],
                            tool_output=tr["output"],
                            is_error=tr["is_error"],
                        )

                    # Also extract preference signals from user messages
                    await self.traffic_learner.on_messages(optimized_messages)
                except Exception as e:
                    logger.debug(f"[{request_id}] Traffic learner: {e}")

            # Memory: Inject context and tools — gated on MemoryDecision.
            # ``inject`` is False under bypass, missing handler, missing
            # user_id, or HEADROOM_MEMORY_INJECTION_MODE in disabled/tool.
            # Pre-PR-this the gate was a raw conjunction that silently
            # ignored bypass; now bypass is honoured here on Anthropic
            # /v1/messages just as on /v1/responses.
            memory_context_injected = False
            memory_tools_injected = False
            if memory_decision.inject:
                # Search and inject memory context
                if self.memory_handler.config.inject_context:
                    try:
                        async with stage_timer.measure("memory_context"):
                            memory_context = await asyncio.wait_for(
                                self.memory_handler.search_and_format_context(
                                    memory_user_id,
                                    optimized_messages,
                                    request_context=memory_request_ctx,
                                    query=MemoryQuery.from_messages(optimized_messages),
                                ),
                                timeout=(
                                    self.config.anthropic_pre_upstream_memory_context_timeout_seconds
                                ),
                            )
                    except asyncio.TimeoutError:
                        memory_context = None
                        logger.info(
                            f"[{request_id}] Memory: Context lookup exceeded "
                            f"{self.config.anthropic_pre_upstream_memory_context_timeout_seconds:.1f}s; "
                            "continuing without it"
                        )
                    try:
                        if memory_context:
                            from headroom.proxy.helpers import (
                                get_memory_injection_mode,
                                log_memory_injection,
                            )

                            injection_mode = get_memory_injection_mode()
                            user_query = extract_user_query(optimized_messages) or ""
                            if injection_mode == "disabled":
                                log_memory_injection(
                                    request_id=request_id,
                                    session_id=session_id,
                                    decision="skipped_disabled",
                                    bytes_injected=0,
                                    query=user_query,
                                )
                            elif is_cache_mode(self.config.mode):
                                # Cache mode: skip injection entirely so the next-turn
                                # prefix bytes remain byte-equal to this turn's bytes.
                                log_memory_injection(
                                    request_id=request_id,
                                    session_id=session_id,
                                    decision="skipped_cache_mode",
                                    bytes_injected=0,
                                    query=user_query,
                                )
                            else:
                                # P0-1 fix: route exclusively to the live zone tail
                                # (latest non-frozen user turn). System prompt + frozen
                                # prefix are never mutated — invariant I2.
                                before = optimized_messages
                                optimized_messages = (
                                    self._append_context_to_latest_non_frozen_user_turn(
                                        optimized_messages,
                                        memory_context,
                                        frozen_message_count=frozen_message_count,
                                    )
                                )
                                if optimized_messages is not before:
                                    memory_context_injected = True
                                    log_memory_injection(
                                        request_id=request_id,
                                        session_id=session_id,
                                        decision="injected_live_zone_tail",
                                        bytes_injected=len(memory_context),
                                        query=user_query,
                                    )
                                else:
                                    log_memory_injection(
                                        request_id=request_id,
                                        session_id=session_id,
                                        decision="no_eligible_user_turn",
                                        bytes_injected=0,
                                        query=user_query,
                                    )
                    except Exception as e:
                        logger.warning(f"[{request_id}] Memory: Context injection failed: {e}")

                # Inject memory tools — PR-A7 (P0-6) routes through
                # `apply_session_sticky_memory_tools` so tool list bytes
                # stay byte-stable across turns: once a session injects,
                # every subsequent turn replays the same canonical bytes.
                # `inject_this_turn` is True iff memory is enabled this
                # turn (i.e. memory_handler.config.inject_tools and we
                # have a memory_user_id, which the outer guard at line
                # 1192 already enforces).
                from headroom.proxy.helpers import (
                    apply_session_sticky_memory_tools,
                )

                memory_tool_defs = (
                    self.memory_handler.compute_memory_tool_definitions("anthropic")
                    if self.memory_handler.config.inject_tools
                    else []
                )
                tools, mem_tools_injected = apply_session_sticky_memory_tools(
                    provider="anthropic",
                    session_id=session_id,
                    request_id=request_id,
                    existing_tools=tools,
                    memory_tools_to_inject=memory_tool_defs,
                    inject_this_turn=bool(self.memory_handler.config.inject_tools),
                )
                if mem_tools_injected:
                    memory_tools_injected = True
                    tool_names = [
                        t.get("name") or t.get("type", "")
                        for t in tools
                        if t.get("name", "").startswith("memory")
                        or t.get("type", "").startswith("memory")
                    ]
                    logger.info(f"[{request_id}] Memory: Injected tools: {tool_names}")

                    # Add beta headers for native memory tool. PR-A6
                    # (P5-50): use the deterministic `merge_anthropic_beta`
                    # helper instead of ad-hoc string concat. Order:
                    # client tokens first (preserved from session-sticky
                    # baseline above), then Headroom-required tokens.
                    # The session tracker already recorded the client
                    # value; we append Headroom-required tokens here so
                    # the next turn re-applies them deterministically.
                    beta_headers = self.memory_handler.get_beta_headers()
                    if beta_headers:
                        from headroom.proxy.helpers import (
                            log_beta_header_merge as _log_beta_header_merge_mem,
                        )
                        from headroom.proxy.helpers import (
                            merge_anthropic_beta,
                        )

                        for key, value in beta_headers.items():
                            if key.lower() != "anthropic-beta":
                                # Defensive: memory handler currently
                                # only emits anthropic-beta. Any future
                                # provider-specific beta header would
                                # need its own merge helper.
                                headers[key] = value
                                continue
                            existing_value = headers.get(key, "")
                            required_tokens = [t.strip() for t in value.split(",") if t.strip()]
                            merged = merge_anthropic_beta(existing_value, required_tokens)
                            _existing_count = (
                                len([t for t in existing_value.split(",") if t.strip()])
                                if existing_value
                                else 0
                            )
                            _merged_count = (
                                len([t for t in merged.split(",") if t.strip()]) if merged else 0
                            )
                            headers[key] = merged
                            _log_beta_header_merge_mem(
                                provider="anthropic",
                                session_id=session_id,
                                client_betas_count=_existing_count,
                                sticky_betas_count=_merged_count,
                                headroom_added=required_tokens,
                                request_id=request_id,
                            )
                            logger.info(f"[{request_id}] Memory: Added beta header: {key}={merged}")

            if memory_context_injected or memory_tools_injected:
                remembered_event = self.pipeline_extensions.emit(
                    PipelineStage.INPUT_REMEMBERED,
                    operation="proxy.request",
                    request_id=request_id,
                    provider="anthropic",
                    model=model,
                    messages=optimized_messages,
                    tools=tools,
                    headers=headers,
                    metadata={
                        "memory_context_injected": memory_context_injected,
                        "memory_tools_injected": memory_tools_injected,
                    },
                )
                if remembered_event.messages is not None:
                    optimized_messages = remembered_event.messages
                if remembered_event.tools is not None:
                    tools = remembered_event.tools
                if remembered_event.headers is not None:
                    headers = remembered_event.headers

            # Update body
            body["messages"] = optimized_messages
            if tools is not None:
                tools = self._sort_tools_deterministically(tools)
                body["tools"] = tools

            presend_event = self.pipeline_extensions.emit(
                PipelineStage.PRE_SEND,
                operation="proxy.request",
                request_id=request_id,
                provider="anthropic",
                model=model,
                messages=optimized_messages,
                tools=tools,
                headers=headers,
                metadata={"path": "/v1/messages", "stream": stream},
            )
            previous_presend_messages = optimized_messages
            if presend_event.messages is not None:
                optimized_messages = presend_event.messages
                body["messages"] = optimized_messages
            if presend_event.tools is not None:
                tools = self._sort_tools_deterministically(presend_event.tools)
                body["tools"] = tools
            if presend_event.headers is not None:
                headers = presend_event.headers
            if presend_event.messages is not previous_presend_messages:
                optimized_tokens = tokenizer.count_messages(body["messages"])
                tokens_saved = max(0, original_tokens - optimized_tokens)

            # Unit 2: mark end of pre-upstream phase. Everything after this
            # point is upstream I/O or post-response bookkeeping.
            stage_timer.record(
                "total_pre_upstream",
                (time.perf_counter() - pre_upstream_started_at) * 1000.0,
            )

            # Byte-faithful forwarder support (PR-A3, fixes P0-2). At this
            # point body has been through every transform (image, compression,
            # memory, tool sort, pipeline extensions). If a transform reported
            # it touched the body, mark mutated; we additionally compare the
            # final body against the parsed original bytes as a structural
            # safety net so any silent mutation we missed still triggers
            # canonical re-serialization.
            if not body_mutation_tracker.mutated and original_body_bytes is not None:
                try:
                    parsed_original = json.loads(original_body_bytes)
                    if parsed_original != body:
                        body_mutation_tracker.mark_mutated("structural_diff_vs_original")
                except (json.JSONDecodeError, ValueError):
                    body_mutation_tracker.mark_mutated("original_unparseable")

            # Forward request - use Bedrock backend if configured, otherwise direct API
            if self.anthropic_backend is not None:
                # Route through Bedrock backend
                try:
                    if stream:
                        self.pipeline_extensions.emit(
                            PipelineStage.POST_SEND,
                            operation="proxy.request",
                            request_id=request_id,
                            provider="anthropic",
                            model=model,
                            messages=body["messages"],
                            tools=tools,
                            metadata={"path": "/v1/messages", "stream": True},
                        )
                        await _finalize_pre_upstream()
                        return await self._stream_response_bedrock(
                            body,
                            headers,
                            "anthropic",
                            model,
                            request_id,
                            original_tokens,
                            optimized_tokens,
                            tokens_saved,
                            transforms_applied,
                            tags,
                            optimization_latency,
                            pipeline_timing=pipeline_timing,
                        )
                    else:
                        async with stage_timer.measure("upstream_connect"):
                            backend_response = await self.anthropic_backend.send_message(
                                body, headers
                            )
                        self.pipeline_extensions.emit(
                            PipelineStage.POST_SEND,
                            operation="proxy.request",
                            request_id=request_id,
                            provider="anthropic",
                            model=model,
                            messages=body["messages"],
                            tools=tools,
                            response=backend_response.body,
                            metadata={
                                "path": "/v1/messages",
                                "stream": False,
                                "status_code": backend_response.status_code,
                            },
                        )
                        self.pipeline_extensions.emit(
                            PipelineStage.RESPONSE_RECEIVED,
                            operation="proxy.request",
                            request_id=request_id,
                            provider="anthropic",
                            model=model,
                            response=backend_response.body,
                            metadata={
                                "path": "/v1/messages",
                                "stream": False,
                                "status_code": backend_response.status_code,
                            },
                        )
                        # Non-stream: first-byte and connect are effectively
                        # the same horizon — ``send_message`` awaits until
                        # the response body is fully buffered.
                        if (
                            "upstream_first_byte" not in stage_timer
                            and "upstream_connect" in stage_timer
                        ):
                            stage_timer.record(
                                "upstream_first_byte",
                                stage_timer.summary()["upstream_connect"],
                            )
                        await _finalize_pre_upstream()
                        if backend_response.error:
                            return JSONResponse(
                                status_code=backend_response.status_code,
                                content=backend_response.body,
                            )

                        # Track metrics
                        total_latency = (time.time() - start_time) * 1000
                        usage = backend_response.body.get("usage", {})
                        output_tokens = usage.get("output_tokens", 0)

                        _backend_name = (
                            self.anthropic_backend.name if self.anthropic_backend else "anthropic"
                        )
                        # Eligible-only denominator for the active
                        # compression ratio: tokens in the live zone we
                        # actually attempted to compress. Frozen prefix
                        # (system + prior cached turns) is byte-identical
                        # pre/post — counting it would dilute the metric
                        # with content we deliberately don't touch for
                        # prefix-cache safety. Fall back to the full
                        # pre-comp request if the live-zone count fails
                        # so the aggregate denominator stays coherent.
                        try:
                            attempted_input_tokens = tokenizer.count_messages(
                                original_client_messages[frozen_message_count:]
                            )
                        except Exception:
                            attempted_input_tokens = original_tokens
                        # Backend (Bedrock / Vertex) non-streaming.
                        # Cache metrics aren't extracted from the backend
                        # response here yet — that's a follow-up. The
                        # funnel passes 0s for the cache fields, which
                        # is the same observable behaviour as the
                        # pre-refactor code (which also omitted them).
                        await self._record_request_outcome(
                            RequestOutcome(
                                request_id=request_id,
                                provider=_backend_name,
                                model=model,
                                original_tokens=original_tokens,
                                optimized_tokens=optimized_tokens,
                                output_tokens=output_tokens,
                                tokens_saved=tokens_saved,
                                attempted_input_tokens=attempted_input_tokens,
                                total_latency_ms=total_latency,
                                overhead_ms=optimization_latency,
                                pipeline_timing=pipeline_timing,
                                transforms_applied=tuple(transforms_applied),
                                num_messages=len(body.get("messages", [])),
                                tags=tags,
                                client=client,
                                turn_id=compute_turn_id(
                                    model, body.get("system"), body.get("messages")
                                ),
                                request_messages=body.get("messages")
                                if self.config.log_full_messages
                                else None,
                            )
                        )

                        return JSONResponse(
                            status_code=backend_response.status_code,
                            content=backend_response.body,
                        )
                except Exception as e:
                    logger.error(f"[{request_id}] Bedrock backend error: {e}")
                    # Unit 4: release the pre-upstream semaphore on error.
                    await _finalize_pre_upstream()
                    return JSONResponse(
                        status_code=500,
                        content={
                            "type": "error",
                            "error": {"type": "api_error", "message": str(e)},
                        },
                    )

            # Direct Anthropic API
            url = f"{self.ANTHROPIC_API_URL}/v1/messages"

            try:
                if stream:
                    self.pipeline_extensions.emit(
                        PipelineStage.POST_SEND,
                        operation="proxy.request",
                        request_id=request_id,
                        provider="anthropic",
                        model=model,
                        messages=body["messages"],
                        tools=tools,
                        metadata={"path": "/v1/messages", "stream": True},
                    )
                    await _finalize_pre_upstream()
                    return await self._stream_response(
                        url,
                        headers,
                        body,
                        "anthropic",
                        model,
                        request_id,
                        original_tokens,
                        optimized_tokens,
                        tokens_saved,
                        transforms_applied,
                        tags,
                        optimization_latency,
                        memory_user_id=memory_user_id,
                        pipeline_timing=pipeline_timing,
                        prefix_tracker=prefix_tracker,
                        original_messages=original_client_messages,
                        original_body_bytes=original_body_bytes,
                        body_mutated=body_mutation_tracker.mutated,
                        mutation_reasons=body_mutation_tracker.reasons,
                        memory_request_ctx=memory_request_ctx,
                    )
                else:
                    async with stage_timer.measure("upstream_connect"):
                        response = await self._retry_request(
                            "POST",
                            url,
                            headers,
                            body,
                            original_body_bytes=original_body_bytes,
                            body_mutated=body_mutation_tracker.mutated,
                            mutation_reasons=body_mutation_tracker.reasons,
                            request_id=request_id,
                            forwarder_name="anthropic_messages",
                            path_for_log="/v1/messages",
                        )
                    self.pipeline_extensions.emit(
                        PipelineStage.POST_SEND,
                        operation="proxy.request",
                        request_id=request_id,
                        provider="anthropic",
                        model=model,
                        messages=body["messages"],
                        tools=tools,
                        response=response,
                        metadata={
                            "path": "/v1/messages",
                            "stream": False,
                            "status_code": response.status_code,
                        },
                    )
                    self.pipeline_extensions.emit(
                        PipelineStage.RESPONSE_RECEIVED,
                        operation="proxy.request",
                        request_id=request_id,
                        provider="anthropic",
                        model=model,
                        response=response,
                        metadata={
                            "path": "/v1/messages",
                            "stream": False,
                            "status_code": response.status_code,
                        },
                    )
                    if (
                        "upstream_first_byte" not in stage_timer
                        and "upstream_connect" in stage_timer
                    ):
                        stage_timer.record(
                            "upstream_first_byte",
                            stage_timer.summary()["upstream_connect"],
                        )
                    await _finalize_pre_upstream()
                    # Full diagnostic dump on upstream errors.
                    # Writes pre/post compression messages, tools, and error
                    # to ~/.headroom/logs/debug_400/ for offline analysis.
                    if response.status_code >= 400:
                        try:
                            err_body = response.json()
                            err_msg = err_body.get("error", {}).get("message", "")
                            err_type = err_body.get("error", {}).get("type", "")
                        except Exception:
                            err_body = {"raw": response.text[:2000]}
                            err_msg = str(response.text[:500])
                            err_type = "parse_error"

                        logger.warning(
                            f"[{request_id}] UPSTREAM_ERROR "
                            f"status={response.status_code} "
                            f"error_type={err_type} "
                            f"error_msg={err_msg!r} "
                            f"model={model} "
                            f"compressed={'yes' if transforms_applied else 'no'} "
                            f"transforms={transforms_applied} "
                            f"original_tokens={original_tokens} "
                            f"optimized_tokens={optimized_tokens} "
                            f"message_count={len(body.get('messages', []))} "
                            f"stream={stream}"
                        )

                        # Dump full request details to debug file
                        try:
                            from headroom import paths as _hr_paths

                            debug_dir = _hr_paths.debug_400_dir()
                            debug_dir.mkdir(parents=True, exist_ok=True)
                            ts = datetime.now().strftime("%Y%m%d_%H%M%S")
                            debug_file = debug_dir / f"{ts}_{request_id}.json"

                            # Sanitize headers (redact API keys)
                            safe_headers = {}
                            for k, v in headers.items():
                                if k.lower() in ("x-api-key", "authorization"):
                                    safe_headers[k] = v[:12] + "..." if v else ""
                                else:
                                    safe_headers[k] = v

                            debug_payload = {
                                "request_id": request_id,
                                "timestamp": datetime.now().isoformat(),
                                "status_code": response.status_code,
                                "error_response": err_body,
                                "model": model,
                                "stream": stream,
                                "headers": safe_headers,
                                "compression": {
                                    "was_compressed": bool(transforms_applied),
                                    "transforms": transforms_applied,
                                    "original_tokens": original_tokens,
                                    "optimized_tokens": optimized_tokens,
                                    "tokens_saved": tokens_saved,
                                    "compression_failed": _compression_failed,
                                },
                                "tools_sent": body.get("tools"),
                                "tool_count": len(body.get("tools") or []),
                                "original_tool_count": len(_original_tools or []),
                                "messages_sent": body.get("messages"),
                                "message_count": len(body.get("messages", [])),
                                "original_messages": (
                                    original_messages
                                    if original_messages is not body.get("messages")
                                    else "__same_as_sent__"
                                ),
                                "original_message_count": len(original_messages),
                                "system_prompt": body.get("system"),
                            }

                            with open(debug_file, "w") as f:
                                json.dump(debug_payload, f, indent=2, default=str)

                            logger.warning(f"[{request_id}] Full debug dump: {debug_file}")
                        except Exception as dump_err:
                            logger.error(f"[{request_id}] Failed to write debug dump: {dump_err}")

                    # Parse response for CCR handling
                    resp_json = None
                    try:
                        resp_json = response.json()
                    except (json.JSONDecodeError, ValueError) as e:
                        logger.debug(
                            f"[{request_id}] Failed to parse response JSON for CCR handling: {e}"
                        )

                    # CCR Response Handling: Handle headroom_retrieve tool calls automatically
                    if (
                        self.ccr_response_handler
                        and resp_json
                        and response.status_code == 200
                        and self.ccr_response_handler.has_ccr_tool_calls(resp_json, "anthropic")
                    ):
                        logger.info(
                            f"[{request_id}] CCR: Detected retrieval tool call, handling..."
                        )

                        # Create API call function for continuation
                        # Use a fresh client to avoid potential decompression state issues
                        async def api_call_fn(
                            msgs: list[dict], tls: list[dict] | None
                        ) -> dict[str, Any]:
                            continuation_body = {
                                **body,
                                "messages": msgs,
                            }
                            if tls is not None:
                                continuation_body["tools"] = tls

                            # Use clean headers for continuation
                            continuation_headers = {
                                k: v
                                for k, v in headers.items()
                                if k.lower()
                                not in (
                                    "content-encoding",
                                    "transfer-encoding",
                                    "accept-encoding",
                                    "content-length",
                                )
                            }

                            # Reuse main client for CCR continuations (connection pooling)
                            logger.info(
                                f"CCR: Making continuation request with {len(msgs)} messages"
                            )
                            assert self.http_client is not None, "HTTP client not initialized"
                            # Byte-faithful (PR-A3, fixes P0-2). The CCR
                            # continuation body is synthesized by Headroom
                            # so it is treated as mutated and goes through
                            # the canonical serializer.
                            from headroom.proxy.helpers import (
                                log_outbound_request,
                                prepare_outbound_body_bytes,
                            )

                            ccr_outbound_bytes, ccr_outbound_source = prepare_outbound_body_bytes(
                                body=continuation_body,
                                original_body_bytes=None,
                                body_mutated=True,
                            )
                            ccr_outbound_headers = {
                                **continuation_headers,
                                "content-type": "application/json",
                            }
                            log_outbound_request(
                                forwarder="anthropic_ccr_continuation",
                                method="POST",
                                path=url,
                                body_bytes_count=len(ccr_outbound_bytes),
                                body_mutated=True,
                                mutation_reasons=["ccr_continuation"],
                                request_id=request_id,
                                source=ccr_outbound_source,
                            )
                            try:
                                cont_response = await self.http_client.post(
                                    url,
                                    content=ccr_outbound_bytes,
                                    headers=ccr_outbound_headers,
                                    timeout=httpx.Timeout(120.0),  # Override timeout for CCR
                                )
                                logger.info(
                                    f"CCR: Got response status={cont_response.status_code}, "
                                    f"content-encoding={cont_response.headers.get('content-encoding')}"
                                )
                                result: dict[str, Any] = cont_response.json()
                                logger.info("CCR: Parsed JSON successfully")
                                return result
                            except Exception as e:
                                resp_headers: str | dict[str, str] = "N/A"
                                try:
                                    resp_headers = dict(cont_response.headers)
                                except Exception:
                                    pass
                                logger.error(
                                    f"CCR: API call failed: {e}, response headers: {resp_headers}"
                                )
                                raise

                        # Handle CCR tool calls
                        try:
                            final_resp_json = await self.ccr_response_handler.handle_response(
                                resp_json,
                                optimized_messages,
                                tools,
                                api_call_fn,
                                provider="anthropic",
                            )
                            # Update response content with final response
                            resp_json = final_resp_json
                            # Remove encoding headers since content is now uncompressed JSON
                            ccr_response_headers = {
                                k: v
                                for k, v in response.headers.items()
                                if k.lower() not in ("content-encoding", "content-length")
                            }
                            try:
                                ccr_content = json.dumps(final_resp_json).encode()
                            except (TypeError, ValueError) as json_err:
                                logger.warning(
                                    f"[{request_id}] CCR: JSON serialization failed: {json_err}"
                                )
                                ccr_content = json.dumps(resp_json).encode()
                            response = httpx.Response(
                                status_code=200,
                                content=ccr_content,
                                headers=ccr_response_headers,
                            )
                            logger.info(f"[{request_id}] CCR: Retrieval handled successfully")
                        except Exception as e:
                            import traceback

                            logger.warning(
                                f"[{request_id}] CCR: Response handling failed: {e}\n"
                                f"Traceback: {traceback.format_exc()}"
                            )
                            # Continue with original response

                    # Memory: Handle memory tool calls in response
                    if (
                        self.memory_handler
                        and memory_user_id
                        and resp_json
                        and response.status_code == 200
                        and self.memory_handler.has_memory_tool_calls(resp_json, "anthropic")
                    ):
                        logger.info(
                            f"[{request_id}] Memory: Detected memory tool call, handling..."
                        )

                        try:
                            # Execute memory tool calls
                            tool_results = await self.memory_handler.handle_memory_tool_calls(
                                resp_json,
                                memory_user_id,
                                "anthropic",
                                request_context=memory_request_ctx,
                            )

                            if tool_results:
                                # Create continuation messages
                                assistant_msg = {
                                    "role": "assistant",
                                    "content": resp_json.get("content", []),
                                }
                                user_msg = {
                                    "role": "user",
                                    "content": tool_results,
                                }

                                continuation_messages = optimized_messages + [
                                    assistant_msg,
                                    user_msg,
                                ]

                                # Make continuation API call
                                continuation_body = {**body, "messages": continuation_messages}
                                if tools:
                                    continuation_body["tools"] = tools

                                cont_response = await self._retry_request(
                                    "POST", url, headers, continuation_body
                                )

                                # Update response with continuation
                                resp_json = cont_response.json()
                                response = cont_response
                                logger.info(
                                    f"[{request_id}] Memory: Tool calls handled, continuation complete"
                                )

                        except Exception as e:
                            logger.warning(f"[{request_id}] Memory: Tool call handling failed: {e}")
                            # Continue with original response

                    total_latency = (time.time() - start_time) * 1000

                    # Parse response for output token count and cache metrics
                    output_tokens = 0
                    cr_tokens = 0
                    cw_tokens = 0
                    cw_5m_tokens = 0
                    cw_1h_tokens = 0
                    uncached_input_tokens = 0
                    if resp_json:
                        usage = resp_json.get("usage", {})
                        output_tokens = usage.get("output_tokens", 0)
                        cr_tokens = usage.get("cache_read_input_tokens", 0)
                        cw_tokens = usage.get("cache_creation_input_tokens", 0)
                        cw_5m_tokens, cw_1h_tokens = self._extract_anthropic_cache_ttl_metrics(
                            usage
                        )
                        uncached_input_tokens = usage.get("input_tokens", 0)

                    # Track cache bust: tokens that lost their cache discount due to compression.
                    # If we had X tokens cached last turn and only Y hit cache this turn,
                    # then (X - Y) tokens were busted by our modifications.
                    expected_cached = prefix_tracker._cached_token_count
                    if expected_cached > 0 and tokens_saved > 0:
                        bust_tokens = max(0, expected_cached - cr_tokens)
                        if bust_tokens > 0:
                            logger.info(
                                f"[{request_id}] CACHE-BUST: "
                                f"expected_cached={expected_cached:,} actual_read={cr_tokens:,} "
                                f"tokens_lost={bust_tokens:,} tokens_saved={tokens_saved:,}"
                            )
                            await self.metrics.record_cache_bust(bust_tokens)

                    # Update prefix cache tracker for next turn
                    next_original_messages = copy.deepcopy(original_client_messages)
                    next_forwarded_messages = copy.deepcopy(optimized_messages)
                    assistant_message = self._assistant_message_from_response_json(resp_json)
                    if assistant_message is not None:
                        next_original_messages.append(copy.deepcopy(assistant_message))
                        next_forwarded_messages.append(copy.deepcopy(assistant_message))
                    prefix_tracker.update_from_response(
                        cache_read_tokens=cr_tokens,
                        cache_write_tokens=cw_tokens,
                        messages=next_forwarded_messages,
                        original_messages=next_original_messages,
                    )

                    # Cache response
                    if self.cache and response.status_code == 200:
                        await self.cache.set(
                            messages,
                            model,
                            response.content,
                            dict(response.headers),
                            tokens_saved=tokens_saved,
                        )

                    # Subscription tracker: update headroom contribution
                    # counters. Provider-specific OAuth/subscription
                    # accounting — stays outside the funnel (different
                    # concern, only fires for Bearer-not-sk-ant tokens).
                    if _auth_header.startswith("Bearer ") and not _auth_header.startswith(
                        "Bearer sk-ant-api"
                    ):
                        from headroom.subscription.tracker import (
                            get_subscription_tracker as _get_sub_tracker,
                        )

                        _sub_tracker = _get_sub_tracker()
                        if _sub_tracker is not None:
                            _sub_tracker.update_contribution(
                                tokens_submitted=optimized_tokens,
                                tokens_saved_compression=tokens_saved,
                                tokens_saved_cache_reads=cr_tokens,
                            )

                    # The pre-refactor PERF emit (above) read raw usage
                    # off ``resp_usage`` instead of trusting cr_tokens /
                    # cw_tokens. Both paths land on identical numbers
                    # (extraction happens just above the cost_tracker
                    # call), so the funnel uses the already-computed
                    # values for consistency. Pre-refactor's
                    # ``cache_hit`` local was correctly derived from
                    # cache_read>0; the funnel re-derives via the
                    # outcome property — same result.
                    #
                    # ``attempted_input_tokens`` was MISSING from the
                    # pre-refactor record_request call here (one of the
                    # 7-of-18 sites the P0 audit flagged). The funnel
                    # forces it to a value — using
                    # ``optimized_tokens + tokens_saved`` as the
                    # fallback denominator, same as the streaming path
                    # uses (see _finalize_stream_response). Dashboards
                    # that were showing 0% active-savings on non-
                    # streaming Anthropic traffic will now show the
                    # correct ratio.
                    await self._record_request_outcome(
                        RequestOutcome(
                            request_id=request_id,
                            provider="anthropic",
                            model=model,
                            original_tokens=original_tokens,
                            optimized_tokens=optimized_tokens,
                            output_tokens=output_tokens,
                            tokens_saved=tokens_saved,
                            attempted_input_tokens=optimized_tokens + tokens_saved,
                            cache_read_tokens=cr_tokens,
                            cache_write_tokens=cw_tokens,
                            cache_write_5m_tokens=cw_5m_tokens,
                            cache_write_1h_tokens=cw_1h_tokens,
                            uncached_input_tokens=uncached_input_tokens,
                            total_latency_ms=total_latency,
                            overhead_ms=optimization_latency,
                            pipeline_timing=pipeline_timing,
                            waste_signals=waste_signals_dict,
                            transforms_applied=tuple(transforms_applied),
                            num_messages=len(messages),
                            tags=tags,
                            client=client,
                            turn_id=compute_turn_id(
                                model, body.get("system"), body.get("messages")
                            ),
                            request_messages=messages if self.config.log_full_messages else None,
                        )
                    )

                    # Remove compression headers since httpx already decompressed the response
                    response_headers = dict(response.headers)
                    response_headers.pop("content-encoding", None)
                    response_headers.pop(
                        "content-length", None
                    )  # Length changed after decompression

                    # Inject Headroom compression metrics (for SaaS metering)
                    response_headers["x-headroom-tokens-before"] = str(original_tokens)
                    response_headers["x-headroom-tokens-after"] = str(optimized_tokens)
                    response_headers["x-headroom-tokens-saved"] = str(tokens_saved)
                    response_headers["x-headroom-model"] = model
                    if transforms_applied:
                        response_headers["x-headroom-transforms"] = ",".join(transforms_applied)
                    if cache_hit:
                        response_headers["x-headroom-cached"] = "true"
                    if _compression_failed:
                        response_headers["x-headroom-compression-failed"] = "true"

                    # Enterprise Security: scan response + de-anonymize
                    if self.security and _security_ctx and resp_json:
                        try:
                            resp_json = self.security.scan_response(resp_json, _security_ctx)
                            response = httpx.Response(
                                status_code=200,
                                content=json.dumps(resp_json).encode(),
                                headers=response_headers,
                            )
                            return Response(
                                content=response.content,
                                status_code=response.status_code,
                                headers=response_headers,
                            )
                        except Exception as sec_err:
                            logger.warning(
                                f"[{request_id}] Security response scan error: {sec_err}"
                            )

                    return Response(
                        content=response.content,
                        status_code=response.status_code,
                        headers=response_headers,
                    )
            except HTTPException:
                # FastAPI HTTPException carries its own status code, headers,
                # and client-facing message (e.g. 429 with Retry-After, 413 for
                # oversized bodies). Let FastAPI's own exception handler produce
                # the response — swallowing it into the 502 catch-all below
                # would regress rate-limit and budget responses to 502 with no
                # Retry-After header. The outer finally still runs.
                raise
            except Exception as e:
                await self.metrics.record_failed(provider="anthropic")
                # Log full error details internally for debugging
                logger.error(f"[{request_id}] Request failed: {type(e).__name__}: {e}")

                # Try fallback if enabled
                if self.config.fallback_enabled and self.config.fallback_provider == "openai":
                    logger.info(f"[{request_id}] Attempting fallback to OpenAI")
                    # Convert to OpenAI format and retry
                    # (simplified - would need message format conversion)

                # Return sanitized error message to client (don't expose internal details)
                return JSONResponse(
                    status_code=502,
                    content={
                        "type": "error",
                        "error": {
                            "type": "api_error",
                            "message": "An error occurred while processing your request. Please try again.",
                        },
                    },
                )
            finally:
                # Unit 2: always emit pre-upstream stage timings exactly
                # once per request, even on early/error paths.
                await _finalize_pre_upstream()
        finally:
            # Unit 4: defense-in-depth. The inner try/finally above
            # already calls this on every normal exit path, but an
            # unexpected exception between the semaphore acquire and the
            # inner try (e.g. AttributeError in a transform, OOM in a
            # deep-copy) would otherwise leak the pre-upstream semaphore
            # permanently. The emit function is idempotent.
            await _finalize_pre_upstream()

    async def handle_anthropic_batch_create(
        self,
        request: Request,
    ) -> Response:
        """Handle Anthropic POST /v1/messages/batches endpoint with compression.

        Anthropic batch format:
        {
            "requests": [
                {
                    "custom_id": "req-1",
                    "params": {
                        "model": "claude-sonnet-4-20250514",
                        "max_tokens": 1024,
                        "messages": [{"role": "user", "content": "Hello"}]
                    }
                },
                ...
            ]
        }

        This method applies compression to each request's messages before forwarding.
        """
        from fastapi.responses import JSONResponse, Response

        from headroom.ccr import CCRToolInjector
        from headroom.proxy.helpers import MAX_REQUEST_BODY_SIZE, _read_request_json
        from headroom.proxy.modes import is_cache_mode
        from headroom.tokenizers import get_tokenizer
        from headroom.utils import extract_user_query

        start_time = time.time()
        request_id = await self._next_request_id()

        # Check request body size
        content_length = request.headers.get("content-length")
        if content_length and int(content_length) > MAX_REQUEST_BODY_SIZE:
            return JSONResponse(
                status_code=413,
                content={
                    "type": "error",
                    "error": {
                        "type": "request_too_large",
                        "message": f"Request body too large. Maximum size is {MAX_REQUEST_BODY_SIZE // (1024 * 1024)}MB",
                    },
                },
            )

        # Parse request
        try:
            body = await _read_request_json(request)
        except (json.JSONDecodeError, ValueError) as e:
            return JSONResponse(
                status_code=400,
                content={
                    "type": "error",
                    "error": {
                        "type": "invalid_request_error",
                        "message": f"Invalid request body: {e!s}",
                    },
                },
            )

        requests_list = body.get("requests", [])
        if not requests_list:
            return JSONResponse(
                status_code=400,
                content={
                    "type": "error",
                    "error": {
                        "type": "invalid_request_error",
                        "message": "Missing or empty 'requests' field in batch request",
                    },
                },
            )

        # Extract headers
        headers = dict(request.headers.items())
        headers.pop("host", None)
        headers.pop("content-length", None)
        client = classify_client(headers)
        tags = extract_tags(headers)
        # PR-A5 (P5-49): strip internal x-headroom-* before forwarding upstream.
        from headroom.proxy.helpers import _strip_internal_headers, log_outbound_headers

        _pre_strip_count = sum(1 for k in headers if k.lower().startswith("x-headroom-"))
        headers = _strip_internal_headers(headers)
        log_outbound_headers(
            forwarder="anthropic_batch",
            stripped_count=_pre_strip_count,
            request_id=request_id,
        )

        # Track compression stats across all batch requests
        total_original_tokens = 0
        total_optimized_tokens = 0
        total_tokens_saved = 0
        compressed_requests = []
        pipeline_timing: dict[str, float] = {}

        # Apply compression to each request in the batch
        for batch_req in requests_list:
            custom_id = batch_req.get("custom_id", "")
            params = batch_req.get("params", {})
            canonical_params = dict(params)
            canonical_tools = canonical_params.get("tools")
            if canonical_tools is not None:
                canonical_params["tools"] = self._sort_tools_deterministically(canonical_tools)
            messages = params.get("messages", [])
            original_messages = copy.deepcopy(messages)
            model = params.get("model", "unknown")

            if not messages or not self.config.optimize:
                # No messages or optimization disabled - pass through unchanged
                compressed_requests.append(
                    {
                        "custom_id": custom_id,
                        "params": canonical_params,
                    }
                )
                continue

            # Apply optimization
            original_tokens = 0  # Initialize before try to prevent UnboundLocalError
            try:
                context_limit = self.anthropic_provider.get_context_limit(model)
                frozen_message_count = (
                    self._strict_previous_turn_frozen_count(original_messages, 0)
                    if is_cache_mode(self.config.mode)
                    else 0
                )
                if is_cache_mode(self.config.mode):
                    optimized_messages = messages
                    original_tokens = get_tokenizer(model).count_messages(messages)
                    optimized_tokens = original_tokens
                else:
                    result = self.anthropic_pipeline.apply(
                        messages=messages,
                        model=model,
                        model_limit=context_limit,
                        context=extract_user_query(messages),
                        frozen_message_count=frozen_message_count,
                        request_id=request_id,
                    )

                    optimized_messages = result.messages
                    for k, v in result.timing.items():
                        pipeline_timing[k] = pipeline_timing.get(k, 0.0) + v
                    # Use pipeline's token counts for consistency with pipeline logs
                    original_tokens = result.tokens_before
                    optimized_tokens = result.tokens_after
                # Guard: if "optimization" inflated tokens, revert to originals
                if optimized_tokens > original_tokens:
                    logger.warning(
                        f"[{request_id}] Batch item optimization inflated tokens "
                        f"({original_tokens} -> {optimized_tokens}), reverting"
                    )
                    optimized_messages = messages
                    optimized_tokens = original_tokens

                total_original_tokens += original_tokens
                total_optimized_tokens += optimized_tokens
                tokens_saved = original_tokens - optimized_tokens
                total_tokens_saved += tokens_saved

                # CCR Tool Injection: Inject retrieval tool if compression occurred
                tools = canonical_params.get("tools")
                if self.config.ccr_inject_tool and tokens_saved > 0:
                    injector = CCRToolInjector(
                        provider="anthropic",
                        inject_tool=True,
                        inject_system_instructions=self.config.ccr_inject_system_instructions,
                    )
                    optimized_messages, tools, was_injected = injector.process_request(
                        optimized_messages, tools
                    )
                    if was_injected:
                        logger.debug(
                            f"[{request_id}] CCR: Injected retrieval tool for batch request '{custom_id}'"
                        )

                # Create compressed batch request
                compressed_params = {**params, "messages": optimized_messages}
                if tools is not None:
                    compressed_params["tools"] = self._sort_tools_deterministically(tools)
                compressed_requests.append(
                    {
                        "custom_id": custom_id,
                        "params": compressed_params,
                    }
                )

                if tokens_saved > 0:
                    logger.debug(
                        f"[{request_id}] Batch request '{custom_id}': "
                        f"{original_tokens:,} -> {optimized_tokens:,} tokens "
                        f"(saved {tokens_saved:,})"
                    )

            except Exception as e:
                logger.warning(
                    f"[{request_id}] Optimization failed for batch request '{custom_id}': {e}"
                )
                # Pass through unchanged on failure
                compressed_requests.append(batch_req)
                total_optimized_tokens += original_tokens

        # Update body with compressed requests
        body["requests"] = compressed_requests

        optimization_latency = (time.time() - start_time) * 1000

        # Forward request to Anthropic
        url = f"{self.ANTHROPIC_API_URL}/v1/messages/batches"

        try:
            # Body is always mutated for batch (compressed requests).
            response = await self._retry_request(
                "POST",
                url,
                headers,
                body,
                body_mutated=True,
                mutation_reasons=["batch_compression"],
                request_id=request_id,
                forwarder_name="anthropic_batch",
                path_for_log="/v1/messages/batches",
            )

            # Batch create: tokens accumulated across all requests in
            # the batch. The funnel records it as a single observation
            # under the synthetic model name "batch" — same as
            # pre-refactor, just routed through the canonical path so
            # batch traffic appears in RequestLog + PERF (it didn't
            # before — sites 4/5/6 were "metrics-only").
            await self._record_request_outcome(
                RequestOutcome(
                    request_id=request_id,
                    provider="anthropic",
                    model="batch",
                    original_tokens=total_original_tokens,
                    optimized_tokens=total_optimized_tokens,
                    output_tokens=0,
                    tokens_saved=total_tokens_saved,
                    attempted_input_tokens=total_optimized_tokens + total_tokens_saved,
                    total_latency_ms=optimization_latency,
                    overhead_ms=optimization_latency,
                    pipeline_timing=pipeline_timing,
                    num_messages=len(compressed_requests),
                    tags=tags,
                    client=client,
                )
            )

            # Log compression stats
            if total_tokens_saved > 0:
                savings_percent = (
                    (total_tokens_saved / total_original_tokens * 100)
                    if total_original_tokens > 0
                    else 0
                )
                logger.info(
                    f"[{request_id}] Batch ({len(compressed_requests)} requests): "
                    f"{total_original_tokens:,} -> {total_optimized_tokens:,} tokens "
                    f"(saved {total_tokens_saved:,}, {savings_percent:.1f}%)"
                )

            # Store batch context for CCR result processing
            if response.status_code == 200 and self.config.ccr_inject_tool:
                try:
                    response_data = response.json()
                    batch_id = response_data.get("id")
                    if batch_id:
                        await self._store_anthropic_batch_context(
                            batch_id,
                            requests_list,
                            headers.get("x-api-key"),
                        )
                except Exception as e:
                    logger.warning(f"[{request_id}] Failed to store batch context: {e}")

            # Remove compression headers
            response_headers = dict(response.headers)
            response_headers.pop("content-encoding", None)
            response_headers.pop("content-length", None)

            return Response(
                content=response.content,
                status_code=response.status_code,
                headers=response_headers,
            )

        except Exception as e:
            await self.metrics.record_failed(provider="anthropic")
            logger.error(f"[{request_id}] Batch request failed: {type(e).__name__}: {e}")
            return JSONResponse(
                status_code=502,
                content={
                    "type": "error",
                    "error": {
                        "type": "api_error",
                        "message": "An error occurred while processing your batch request. Please try again.",
                    },
                },
            )

    async def handle_anthropic_batch_passthrough(
        self,
        request: Request,
        batch_id: str | None = None,
    ) -> Response:
        """Handle Anthropic batch passthrough endpoints.

        Used for:
        - GET /v1/messages/batches - List batches
        - GET /v1/messages/batches/{batch_id} - Get batch
        - GET /v1/messages/batches/{batch_id}/results - Get batch results
        - POST /v1/messages/batches/{batch_id}/cancel - Cancel batch
        """
        from fastapi.responses import Response

        request_id = await self._next_request_id()
        start_time = time.time()
        path = request.url.path
        url = f"{self.ANTHROPIC_API_URL}{path}"

        # Preserve query string parameters (e.g., limit, after_id for list endpoint)
        if request.url.query:
            url = f"{url}?{request.url.query}"

        headers = dict(request.headers.items())
        headers.pop("host", None)
        client = classify_client(headers)
        tags = extract_tags(headers)
        # PR-A5 (P5-49): strip internal x-headroom-* before forwarding upstream.
        from headroom.proxy.helpers import _strip_internal_headers, log_outbound_headers

        _pre_strip_count = sum(1 for k in headers if k.lower().startswith("x-headroom-"))
        headers = _strip_internal_headers(headers)
        log_outbound_headers(
            forwarder="anthropic_batch_passthrough",
            stripped_count=_pre_strip_count,
            request_id=None,
        )

        body = await request.body()

        response = await self.http_client.request(  # type: ignore[union-attr]
            method=request.method,
            url=url,
            headers=headers,
            content=body,
        )

        # Batch passthrough: no compression, no transforms — but we
        # still record the request so dashboards see the upstream call
        # happened. Same funnel as the other 5 anthropic sites.
        latency_ms = (time.time() - start_time) * 1000
        await self._record_request_outcome(
            RequestOutcome(
                request_id=request_id,
                provider="anthropic",
                model="passthrough:batches",
                original_tokens=0,
                optimized_tokens=0,
                output_tokens=0,
                tokens_saved=0,
                attempted_input_tokens=0,
                total_latency_ms=latency_ms,
                tags=tags,
                client=client,
            )
        )

        # Remove compression headers
        response_headers = dict(response.headers)
        response_headers.pop("content-encoding", None)
        response_headers.pop("content-length", None)

        return Response(
            content=response.content,
            status_code=response.status_code,
            headers=response_headers,
        )

    async def _store_anthropic_batch_context(
        self,
        batch_id: str,
        requests_list: list[dict[str, Any]],
        api_key: str | None,
    ) -> None:
        """Store batch context for CCR result processing.

        Args:
            batch_id: The batch ID from the API response.
            requests_list: The original batch requests.
            api_key: The API key for continuation calls.
        """
        from headroom.ccr import BatchContext, BatchRequestContext, get_batch_context_store

        store = get_batch_context_store()
        context = BatchContext(
            batch_id=batch_id,
            provider="anthropic",
            api_key=api_key,
            api_base_url=self.ANTHROPIC_API_URL,
        )

        for batch_req in requests_list:
            custom_id = batch_req.get("custom_id", "")
            params = batch_req.get("params", {})
            context.add_request(
                BatchRequestContext(
                    custom_id=custom_id,
                    messages=params.get("messages", []),
                    tools=params.get("tools"),
                    model=params.get("model", ""),
                    extras={
                        "max_tokens": params.get("max_tokens", 4096),
                        "system": params.get("system"),
                    },
                )
            )

        await store.store(context)
        logger.debug(f"Stored batch context for {batch_id} with {len(requests_list)} requests")

    async def handle_anthropic_batch_results(
        self,
        request: Request,
        batch_id: str,
    ) -> Response:
        """Handle Anthropic batch results with CCR post-processing.

        This endpoint:
        1. Fetches raw results from Anthropic
        2. Detects CCR tool calls in each result
        3. Executes retrieval and makes continuation calls
        4. Returns processed results with complete responses
        """
        from fastapi.responses import Response

        from headroom.ccr import BatchResultProcessor, get_batch_context_store

        request_id = await self._next_request_id()
        start_time = time.time()

        # Forward request to get raw results
        url = f"{self.ANTHROPIC_API_URL}/v1/messages/batches/{batch_id}/results"

        if request.url.query:
            url = f"{url}?{request.url.query}"

        headers = dict(request.headers.items())
        headers.pop("host", None)
        client = classify_client(headers)
        tags = extract_tags(headers)
        # PR-A5 (P5-49): strip internal x-headroom-* before forwarding upstream.
        from headroom.proxy.helpers import _strip_internal_headers, log_outbound_headers

        _pre_strip_count = sum(1 for k in headers if k.lower().startswith("x-headroom-"))
        headers = _strip_internal_headers(headers)
        log_outbound_headers(
            forwarder="anthropic_batch_results",
            stripped_count=_pre_strip_count,
            request_id=None,
        )

        response = await self.http_client.get(url, headers=headers)  # type: ignore[union-attr]

        if response.status_code != 200:
            # Error - pass through
            response_headers = dict(response.headers)
            response_headers.pop("content-encoding", None)
            response_headers.pop("content-length", None)
            return Response(
                content=response.content,
                status_code=response.status_code,
                headers=response_headers,
            )

        # Parse results - Anthropic batch results are JSONL format
        raw_content = response.content.decode("utf-8")
        results = []
        for line in raw_content.strip().split("\n"):
            if line.strip():
                try:
                    results.append(json.loads(line))
                except json.JSONDecodeError:
                    continue

        if not results:
            # No results to process
            response_headers = dict(response.headers)
            response_headers.pop("content-encoding", None)
            response_headers.pop("content-length", None)
            return Response(
                content=response.content,
                status_code=response.status_code,
                headers=response_headers,
            )

        # Check if we have context and CCR processing is enabled
        store = get_batch_context_store()
        batch_context = await store.get(batch_id)

        if batch_context is None or not self.config.ccr_inject_tool:
            # No context or CCR disabled - pass through
            response_headers = dict(response.headers)
            response_headers.pop("content-encoding", None)
            response_headers.pop("content-length", None)
            return Response(
                content=response.content,
                status_code=response.status_code,
                headers=response_headers,
            )

        # Process results with CCR handler
        processor = BatchResultProcessor(self.http_client)  # type: ignore[arg-type]
        processed = await processor.process_results(batch_id, results, "anthropic")

        # Convert back to JSONL format
        processed_lines = []
        for p in processed:
            processed_lines.append(json.dumps(p.result))
            if p.was_processed:
                logger.info(
                    f"CCR: Processed batch result {p.custom_id} "
                    f"({p.continuation_rounds} continuation rounds)"
                )

        processed_content = "\n".join(processed_lines)

        # Batch results, post-CCR processing. Like the other batch
        # sites, no token accounting but we record the request so it's
        # visible in dashboards + headroom perf.
        latency_ms = (time.time() - start_time) * 1000
        await self._record_request_outcome(
            RequestOutcome(
                request_id=request_id,
                provider="anthropic",
                model="batch:ccr-processed",
                original_tokens=0,
                optimized_tokens=0,
                output_tokens=0,
                tokens_saved=0,
                attempted_input_tokens=0,
                total_latency_ms=latency_ms,
                tags=tags,
                client=client,
            )
        )

        return Response(
            content=processed_content.encode("utf-8"),
            status_code=200,
            media_type="application/jsonl",
        )
